Sulfuric Acid → 3,5-Dichloro-4-fluorobenzoic acid

HRID 273455ノート

反応式

HRID 273455 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[F:11])[C:5](Cl)=[O:6].ClC1C=C(C(F)(F)F)C=C(Cl)C=1F.S(=O)(=O)(O)[OH:27].ClS(O)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[F:11])[C:5]([OH:27])=[O:6]

参加物

5

反応物 4

HCID 1118Sulfuric AcidHCID 24638Chlorosulfonic acidHCID 157026Benzene, 1,3-dichloro-2-fluoro-5-(trifluoromethyl)-HCID 196123793,5-Dichloro-4-fluorobenzoyl chloride

生成物 1

HCID 199713033,5-Dichloro-4-fluorobenzoic acid収率 49%

反応条件

温度
80 °C

実験手順

3,5-dichloro-4-fluorobenzoyl chloride can be prepared as follows: To a round bottom flask with nitrogen purge through a 10% aqueous NaOH trap, was added 3,5-dichloro-4-flurobenzotriflouride (5.00 g, 21.46 mmol, Aldrich), concentrated sulfuric acid (4.30 g, 42.92 mmol), and finally chlorosulfonic acid (5.15 g, 43.78 mmol). The reaction began to bubble immediately. After the bubbling subsided, the mixture was heated to 80° C. for 1 hr, cooled to room temperature, and added cautiously to stirred ice water. This was extracted twice with methylene chloride. The combined extracts were washed with water and brine, dried over magnesium sulfate, filtered, and evaporated to give a white solid (2.19 g) of 3,5-dichloro-4-fluorobenzoic acid in 49% yield. 1H-NMR (CD3COCD3, 300 MHz) δ (ppm): 7.95 (d, 2H).

後処理

  1. customTo a round bottom flask with nitrogen purge through a 10% aqueous NaOH trap
  2. customto bubble immediately
  3. temperaturecooled to room temperature
  4. additionadded cautiously
  5. extractionThis was extracted twice with methylene chloride
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-d3ccf74b25a74ec3bd3b7646685b8311
出典データセット
uspto-grants-2008_11
特許番号
US07456315B2

反応ノート

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